


Jake from Indianopolis

by Polly_Phemus (orphan_account)



Series: Everything's Jake [4]
Category: Supernatural
Genre: Boyfriend Experience, Kissing, M/M, Oral Sex, Prostitution, Rimming
Language: English
Status: Completed
Published: 2017-07-27
Updated: 2017-07-27
Packaged: 2018-12-06 05:32:44
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,616
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11593962
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/Polly_Phemus
Summary: Dean's desperate for money.  This Jake's just desperate.





	Jake from Indianopolis

In Indianapolis, Dean was getting desperate. He was midway through what should have been a routine werewolf problem which had been complicated by the vengeful spirit of said werewolf's ex-wife. It wasn't too complicated for Dean...or it wouldn't have been if he had enough money to cover the extra days he was spending dealing with this bullshit.

He went out early; it wasn't even six yet, but there was a bar across the street from his motel and it seemed as good a place as any to start. He got a beer and asked about the state of the tables.

"Monday. League night," the bartender told him. Dean's shoulders slumped. Of course. Being able to hustle up a game so close to his motel would've been too easy on a day like he was having.

"I hate Mondays," he said morosely into his beer.

"Cheer up, Garfield," a man said. He'd appeared suddenly just a couple of stools down from Dean. Dean looked at him: forty-five, pleasant enough looking guy with sandy hair, brown eyes and a friendly smile.

Dean returned the smile. "Dunno," he said. "Don't especially like lasagna, but man, that Odie is a pain in the ass."

The grinned. "It's a push," he said. "And if you don't like lasagna, what do you like?"

"Steak," Dean said immediately. "Or a cheeseburger. Beef, anyway."

"There's a Black Angus not far from here," the guy said. Dean just looked at him. "My treat," he added. Dean kept looking at him. "Look, I just...I hate eating alone," the guy said.

"Okay," Dean said. The guy let out a breath. "Just let me go home, or rather to the Roach Motel across the street, and get cleaned up, dress up a little, and I'll meet you there."

"I...uh...I really appreciate it," the guy said.

"It's kind of...like what I do already. When there's no pool," Dean said. The man's eyebrows shot up. "That an issue?" Dean asked.

"No," the guy said, "it's just that...well, if you're looking for more than dinner...."

"Yeah?" Dean asked, hoping the next thing the guy said wasn't something that could get him arrested for solicitation if he didn't immediately say no.

"Boyfriend experience," the guy said. "That's it."

"Okay," Dean said. "If that's it."

"Right now," the guy said with touching honesty, "it's everything."

"Rough time?"

"The roughest," the guy said. Dean refrained from laughing in his face. The guy had twenty-five years on him and Dean still doubted that he'd lose a so-you-think-your-life-sucks contest to him.

"Okay," Dean said and finished his beer. "I'll see you at Black Angus in an hour, okay? I'm Dean, by the way," he added, seeing no reason not to give the guy his real name. 

"I'm --"

Dean cut him off. "Give you a discount if I can call you Jake, okay?"

The guy laughed. "Sure."

An hour later, Dean, freshly shaved and showered and wearing a suit, showed up at Black Angus.

"I'm Dean. Is Jake here yet?" Dean looked around. The restaurant wasn't crowded with people, but it was still a tight squeeze, with dozens of booths that were so secluded they were almost like little rooms. He was glad he wasn't on a hunt in a place like this.

The hostess, a pretty brunette about Dean's age nodded. "Right this way," she told him, leading him through a dimply lit warren. Dean stopped himself from checking her ass out. He was supposed to give Jake the dream of the "boyfriend experience" not _actual_ boyfriend experience.

Jake's face lit up when he saw Dean. 

"Dean! I'm so glad you're here!"

Dean leaned over to kiss Jake on the cheek. "Of course I am," he murmured. The hostess looked a little shocked.

"Come one," Dean said, giving her half-charm. "I know it's Indiana but it's also practically the twenty-first century."

Dean sat down and the hostess gave them their menus. "Julie will be by to get your drink orders," she said, back to being professionally friendly for a moment before vanishing back to her desk.

Dean made a "got in trouble with the teacher" face at Jake, who laughed.

Dinner went well. The food was good and Jake did most of the talking. All Dean had to do was keep nodding a try to keep up. Jake was obviously a pretty lonely guy who wasn't much used to talking to people; the monologuing would probably drive most people barefoot up a wall but Dean was good with it. If the guy was talking he wasn't asking questions. And he had a pleasant voice. His enthusiasm was endearing even if Dean didn't get most of what he was saying.

Mostly he seemed to be really into some local science fiction writer, so Dean just kept asking questions about that. That got them all the way through dessert.

"So," Dean said as Jake settled the bill, "can a boyfriend see you home? Maybe even a bit more?"

"That would be lovely," Jake said. Lovely wasn't a word Dean heard often but coming from Jake, it sounded natural. 

Jake's place was in a rather cookie-cutter high-rise building, but his apartment itself was attractive. Homey and comfortable, books everywhere, lots of potted plants, the sort of furniture that looked like he'd been picked it out carefully over the years until it all fit together in a space that was personal and unique. Posters for jazz festivals and modern art gallery showings brightened the walls and while it definitely wasn't the kind of place Dean would've thrown together for himself, it was still welcoming.

"There's something on the desk," Jake said. Dean walked over to see a cheap money clip. He didn't count the money; he was sure it was enough for what he needed. He saw a business cart clipped in front of the money and smiled to himself. Jake had used a thick black marker to block out his name while leaving his contact information intact. He'd written "Jake" off to the side. Dean slipped it into his inside jacket pocket before turning around to smile at Jake.

"I've seen you safely to your place," Dean teased Jake. "Does a good boyfriend get a kiss?"

"A boyfriend as good as you gets anything he wants," Jake said. Dean took his hand; it was warm and smooth and Dean couldn't resist running his thumb gently over Jake's palm. Jake shivered a bit as Dean kept rubbing his palm even as he drew them over to Jake's couch.

"Let's take a load off," Dean suggested, pulling Jake to sit next to him. He started kissing Jake, deciding to treat him like he'd treat a girl who wanted him but also liked foreplay. Girls liked boyfriends, even if they were one night stand boyfriends. This was pretty much the same thing, Dean figured, even considering there was money involved.

It was nice. Like the last Jake, the one who liked his bruises, this Jake was a good kisser and it wasn't substantially different from kissing a woman. When it came to kissing, Dean figured, people were people. They each had what they liked and they found a way to let you know.

It could've been a long time they spent kissing or not that much time at all. Dean wasn't watching the clock, but he was keeping an eye on Jake's responses and could tell when it was time to leave or carry things further. Dean found that he wanted to carry things further and not just because it had been a fairly thick stack of bills the money clip was holding together.

"Can we go into the bedroom?" Dean asked. He knew his voice, pitched just so, was close to irresistible in certain circumstances.

"Yeah," Jake said.

The bedroom wasn't that different from the living room: the same hodgepodge of books and personal items, dominated by a queen-sized bed with a patchwork quilt on it. Even though it was high up in the Indianapolis skyline, it made Dean think of a cleaner, tidier version of a room at Bobby's house. 

Dean put those thoughts away to concentrate on Jake. He started undressing them both, alternating between his clothes and Jake's, while Jake stood there, pliant and eager and unbelieving.

Dean could relate. This was not at all how he'd expected his night to go when he'd left his motel looking for a pool game.

Dean retrieved some safety supplies from his pocket, setting them on the floor at the end of the bed before pushing Jake down on the quilt, face up. Dean pulled himself up until he was directly over Jake, nose to nose. 

"You good?" Dean asked.

"The best," Jake said. Dean grinned at him and started kissing. 

He kissed his way gently across Jake's face, avoiding his mouth. He tried the man's ears...that got a groan and a shudder, so he did it again before making his way across Jake's jaw, down his neck, over his heart. Dean lapped at Jake's nipples, easing up when he noticed the faint silver of an old scar on the right one. Bite mark, human, Dean catalogued automatically. Better move past that, whatever it was.

Jake's stomach wasn't exactly pudgy but soft. Not bad for someone who probably read books all day and all of the night. Jake made a sound that seemed more like distress than pleasure, so Dean moved on. He liked Jake's body, but Jake seemed like he maybe didn't, or at least not parts of it, and Dean wasn't there to stress him out.

Which got Dean to Jake's cock. It was a nice cock. Smaller than Dean's in both length and girth but clean and well-proportioned, nicely erect and flushed. Dean touched it and Jake hissed. 

"You like that, baby?" Dean asked. He hoped that was what a boyfriend would say.

"You know I do," Jake said weakly. Dean stroked him. Angle aside, it shouldn't have been that different from jacking himself, except it was really weird to be feeling a cock in his hand without feeling a hand on his cock. Dean tried to keep a steady rhythm while he reached for the floor.

He had to pull his hand off, causing Jake to make a rumbling sound of protest.

"Just give me a sec, okay, babe? Want to get something," Dean said while he fumbled a dental dam out of its wrapper. That done, he lowered his head further, going to his knees at the foot of the bed and pulling Jake forward until his ass was almost at the edge of the bed.

"Gonna eat you out so nice, babe," Dean said. Jake froze, then sat up slightly so he could reach down to bat at Dean's shoulders.

"Dean," Jake protested, "you _know_ how I feel about that."

And, Dean froze, because seriously, what the hell? How was he supposed to know how this Jake feet about anything? Dean remembered just in time: _boyfriend experience_.

"Why don't you remind me?" Dean asked, hoping it was an adequate save.

"I love it," Jake said, his face showing a conflict between desire and what Dean thought looked like shame, "but the scars...."

Jesus, scars? There? Dean closed his eyes for a long moment, cursing himself. He'd assumed that Jake's life had been easier than his own, that it had to have been, with his books and his reading glasses and everything so tidy, but people were never what they seemed, always so much more damaged than the naked eye could assess.

"I don't care about those, baby," Dean said gently. "You know that," he added. It wasn't like he had to look at them and even if he did, scars weren't that big a deal to a hunter although he'd never heard of them in that particular place.

"I...."

"Shh," Dean hushed him. "Just let me do this, you know I love doing this," and, without giving Jake another chance to protest, Dean put the square of latex over Jake and began licking him.

Jake loved getting it, dropping back to the lie flat on the mattress while Dean worked on him. Of course Jake loved it, Dean knew how to use his mouth to please women (although only a couple had let him actually rim them) and while Jake was obviously not a chick, the mechanics weren't all that different. Not like trying to give a blow job.

But...Jake was making the most wonderful, needy noises Dean had heard in a long time. And he was going to need more than just one source of stimulation to have a really good time. And Dean really wanted him to have a good time. And he'd really just been planning to stick with his hand, but....

Dean moved off Jake's ass and licked at his cock. Okay, that was interesting. Definitely not a chick. But...not all that bad.

"No," Jake protested. Dean pulled away from the guy's dick, unable to believe that he was refusing a blow job, however tentative.

"Sorry," Dean said. "I've never...."

"Condom," Jake gasped. "If you want to at all, though, you don't have to...." But Dean heard the man's voice. He didn't have to, but on the other hand, Jake wanted it so much that, yeah, he kinda did.

Dean picked up a condom that he'd automatically put out when he'd gotten the dam out of his wallet and put it on Jake. It was weird, doing it from this angle, but that was exactly the kind of thing Dean could figure that shit out in the dark.

"Got that rascal wrapped," he said and Jake laughed breathlessly. 

Dean went back to giving his first blow job. At first he was worried about doing it wrong, but Jake was not shy about compliments and Dean was soon lost in interpreting what Jake was saying, how his body was reacting, remembering what he himself liked when he was receiving. It wasn't quite as much of a turn on as going down on a woman, but not only was it working for Jake, it was kind of working for Dean and he had enough practice at doing more than one thing at a time that he was able to reach down to take care of himself without shortchanging Jake.

When they'd both come and Dean had removed the condom and cleaned up a little, he hauled himself back up on the bed to cuddle Jake. Jake, at first bonelessly relaxed from orgasm, started to tense up before too long, pulling away from Dean in small moves that were slight but unmistakable.

"I'd better get going," Dean said and Jake didn't protest as Dean got dressed. "Long day tomorrow." The truth was his friend, for once.

"I gave you a card. For if you're back in town," Jake said sleepily.

"Yeah, I got it," Dean said. "If I'm back in town...."

The strange part was that Dean meant it.

The next night, when Dean was getting ready to go out and salt and burn the werewolf's old lady, the motel's desk guy called him over, gave him a box that "your friend dropped off." It was heavy and Dean didn't open it until he was getting ready to leave the next day. A note fell out: 

_Dean,_

_Thank you for a wonderful evening. Here are some books by that writer I was going on and on about last night. You might want to start with_ Cat's Cradle _and go on from there._

_Jake_

Dean mailed the books to himself, care of Bobby but kept out the one called _Cat's Cradle_. It didn't look that long.

**Author's Note:**

>  _Cat's Cradle_ is a frequent recommendation for where to start with Kurt Vonnegut's work (although _Slaughterhouse-Five_ is more likely to be assigned in high school).


End file.
